Acetic Acid → HCID 43560304, compound

HRID 930955Notes

Reaction equation

HRID 930955 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH:9]1([CH:12]=O)[CH2:11][CH2:10]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH2:12][CH:9]1[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 119922-BromoanilineHCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43560304HCID 43560304, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-bromoaniline (1.720 g, 10.00 mmol), cyclopropanecarbaldehyde (0.374 mL, 5.00 mmol), and acetic acid (2.86 mL, 50.0 mmol) in dichloromethane (50 mL) was heated at 50° C. for 1 hour. The solution was cooled in an ice bath and sodium triacetoxyborohydride (2.119 g, 10.00 mmol) was added. This mixture was stirred for 2 hours while warming to ambient temperature and then partitioned between saturated sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-10% ethyl acetate in heptane) to provide the title compound (1.05 g, 93% yield).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. custompartitioned between saturated sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (silica gel, 0-10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-552c44572b4f46cab74a015575fd3ec1
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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